US8337967B2 - Can with bisphenol A capture system - Google Patents
Can with bisphenol A capture system Download PDFInfo
- Publication number
- US8337967B2 US8337967B2 US13/201,607 US201013201607A US8337967B2 US 8337967 B2 US8337967 B2 US 8337967B2 US 201013201607 A US201013201607 A US 201013201607A US 8337967 B2 US8337967 B2 US 8337967B2
- Authority
- US
- United States
- Prior art keywords
- coating
- bisphenol
- metal
- bpa
- electrospun
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 title claims abstract description 200
- 238000000576 coating method Methods 0.000 claims abstract description 108
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- 229910052751 metal Inorganic materials 0.000 claims description 56
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- -1 bisphenol A compound Chemical class 0.000 claims description 48
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- 229910052782 aluminium Inorganic materials 0.000 claims description 9
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Classifications
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- B65B29/00—Packaging of materials presenting special problems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
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- Y10T156/10—Methods of surface bonding and/or assembly therefor
- Y10T156/1002—Methods of surface bonding and/or assembly therefor with permanent bending or reshaping or surface deformation of self sustaining lamina
- Y10T156/1043—Subsequent to assembly
- Y10T156/1044—Subsequent to assembly of parallel stacked sheets only
- Y10T156/1048—Subsequent to assembly of parallel stacked sheets only to form dished or receptacle-like product
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
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Definitions
- Metal cans designed to store food and beverages are typically coated with a polymer to prevent contact between the interior surface of the can and the food or beverage. Such coatings protect the surface of the can from corrosion by the contents of the can and subsequent contamination of the food or beverage.
- Epoxy-based coatings are widely used for this purpose. Many such coatings comprise the chemical compound bisphenol A (2,2-bis(p-hydroxyphenyl)propane; also known as BPA), either as a component of the polymer and/or a plasticizer.
- the present technology provides a bisphenol A capture system for metal cans and other food or beverage containers which include BPA-containing coatings.
- the capture system is made of one or more materials which capture (bind) BPA from the BPA-containing coating.
- the present capture system therefore reduces or prevents BPA from migrating from the can coating into the food or beverages stored in the can.
- the present technology further provides methods of manufacturing and using such coatings.
- a metal which includes an interior surface, wherein at least a portion of the interior surface is covered with one or more of a first coating comprising bisphenol A, and a second coating comprising an electrospun bisphenol A binding material, wherein the first coating is in contact with the interior surface and the second coating is at least partially layered over the first coating.
- the metal may be selected from the group consisting of iron, aluminum, tin, steel, an alloy of any one thereof, and a mixture of any two or more thereof.
- the first coating may be an epoxy resin or polycarbonate resin.
- the second coating is configured to bind substantially all of the bisphenol A leaching from the first coating.
- the electrospun material of the second coating naturally binds bisphenol A.
- Such naturally BPA-binding materials include, e.g., chitin, chitosan, dextrin, fibroin, keratin and mixtures of any two or more thereof.
- the binding material of the second coating has been adapted to binding bisphenol A by molecular imprinting using a bisphenol A compound.
- Such materials include, e.g., cellulose, cellulose acetate, cellulose acetate butylate, lignocellulose, polyamine, N-alkyl acrylamide, N-vinyl pyrrolidone and a mixture of any two or more thereof.
- the present technology provides a metal can including an interior surface wherein at least a portion of the interior surface is coated with a coating comprising bisphenol A and an electrospun material that binds bisphenol A.
- the coating may include, but is not limited to, an epoxy resin or polycarbonate resin.
- the electrospun material may bind substantially all of the bisphenol A in the coating.
- the electrospun material may naturally bind bisphenol A such as where the electrospun material is selected from chitin, chitosan, dextrin, fibroin, keratin and mixtures of any two or more thereof.
- the electrospun material may also be a material adapted to binding bisphenol A by molecular imprinting using bisphenol A or a bisphenol A compound.
- the imprinted electrospun material may be selected from the group consisting of cellulose, cellulose acetate, cellulose acetate butylate, lignocellulose, polyamine, N-alkyl acrylamide, N-vinyl pyrrolidone and a mixture of any two or more thereof.
- the present technology provides a metal can includes an interior surface in which at least a portion of the interior surface is coated with an epoxy resin comprising bisphenol A and an electrospun coating layered over the epoxy resin coating wherein the electrospun coating is selected from cellulose, cellulose acetate, cellulose acetate butylate, or lignocellulose.
- the metal can includes an interior surface coated with an electrospun coating comprising both a BPA-containing polymer and a BPA-binding material.
- the present technology provides methods of manufacturing the bisphenol A capture system described herein.
- the methods include layering an electrospun bisphenol A-binding material onto a coating comprising bisphenol A, wherein the coating covers at least a portion of a metal substrate, such as a metal sheet or a metal can.
- a metal substrate such as a metal sheet or a metal can.
- the methods may further comprise forming a can from the coated metal sheet such that the coating comprises an interior surface of the can.
- formation of the can may take place before or after the layering of the electrospun bisphenol A-binding material onto the coating comprising bisphenol A.
- the methods include forming a first coating comprising bisphenol A on a metal sheet, layering an electrospun bisphenol A-binding material onto the first coating, and forming a can from the coated metal sheet such that the coating comprises an interior surface of the can.
- the methods include layering an electrospun bisphenol A-binding material onto a coating comprising bisphenol A, wherein the coating covers at least a portion of an interior surface of a metal can.
- the metal of the can or sheet may be selected from the group consisting of iron, aluminum, tin, steel, an alloy of any one thereof, and a mixture of any two or more thereof.
- the coating containing BPA may be, e.g., an epoxy resin or polycarbonate resin.
- the electrospun material may be selected from chitin, chitosan, dextrin, fibroin, keratin and mixtures of any two or more thereof.
- the BPA-binding material has been adapted to binding bisphenol A by molecular imprinting using a bisphenol A compound.
- Such materials may be selected from the group consisting of cellulose, cellulose acetate, cellulose acetate butylate, lignocellulose, polyamine, N-alkyl acrylamide, N-vinyl pyrrolidone and a mixture of any two or more thereof.
- the present technology provides methods of using the metal cans comprising the present BPA-capture system.
- such methods include filling any of the cans described herein in whole or in part with a food or beverage.
- the methods include storing a food or beverage in any of the cans described herein.
- FIG. 1 depicts an illustrative embodiment of a can with a BPA capture system of the present technology.
- FIG. 2 depicts an illustrative embodiment of an electrospun surface from C. K. S. Pillai and Chandra P. Sharma, “Electrospinning of Chitin and Chitosan Nanofibres” Trends Biomater. Artif. Organs, 22(3), 179-201 (2009).
- the present technology provides a can with a coating made from one or more materials which bind (capture) BPA and which coating covers (in whole or in part) a BPA-containing coating on the surface of the can.
- the BPA-binding material thus reduces or prevents BPA from migrating from the BPA-containing coating into the contents of the can.
- This BPA-capture coating is formed by electrospinning the BPA-binding material to provide a microporous layer of nanofibers.
- this technology provides an electrospun inner coating over a BPA-containing coating such as an epoxy resin, for food and beverage cans. Because the porous nanofiber layer is hydrophobic, the coating not only captures BPA but also prevents the food or beverage contents from contacting the BPA-containing coating.
- FIG. 1 shows an illustrative embodiment of a can with the BPA-capture system of the present technology.
- the can 10 is made of any suitable metal, e.g., steel, iron, aluminum, tin, an alloy of any one thereof, or a combination of any two or more thereof.
- cans made from combinations of metals include cans in which the end(s) or lids of the cans may be made from a different metal than the bodies of the cans, or one metal (e.g., steel) may be coated with another metal (e.g., tin). While a cylindrical can is shown in FIG. 1 , the present technology is not so limited.
- can may refer to any type of metal container, enclosure, receptacle, or portion thereof that may be used to hold or store a food or beverage and may have any suitable shape.
- the present BPA-capture system may be used with two-piece, three-piece or deep-drawn cans.
- Cans of the present technology include a BPA-containing coating as a first coating on an interior surface(s) of the can ( 20 in FIG. 1 ).
- This BPA-containing coating may be various polymer coatings such as epoxy or polycarbonate, including mixtures or copolymers of epoxy resins such as epoxy-phenolic, epoxy-acrylate, and epoxy-polyester resins.
- Such BPA-containing coatings are known in the art and are commercially available (e.g., D.E.R. 330, D.E.R. 668-20, etc (Dow chemical company, US)) or may be made known methods such as the procedures described in U.S. Pat. Nos. 4,508,765 and 4,179,418, and PCT publication. WO1998/40443, the contents of each of which are incorporated by reference in their entirety herein.
- a metal substrate e.g., a metal sheet to be formed into a can or the preformed can
- a BPA-containing polymer may be coated with various methods known in the art.
- the can may be coated using coil coating or sheet coating operations wherein a planar coil or sheet of the metal substrate is coated with a BPA-containing polymer composition and hardened (e.g., cured).
- the coated substrate then is formed into the can end or body.
- liquid BPA-containing polymer coating compositions may be applied by, e.g., spraying, dipping, rolling, slit coating, etc., to the metal substrate or preformed can and then hardened (e.g., cured).
- Such techniques are described in e.g., U.S. Pat. No. 4,353,934 and U.S. Pat. No. 7,416,758, each of which is incorporated by reference in their entirety herein.
- Epoxy coatings may be hardened using known UV radiation or thermal processes.
- U.S. Pat. No. 4,146,452 (incorporated by reference herein in its entirety) discloses UV curing methods.
- Thermal processes may be carried out using oven-heating, irradiation with infrared light (IR drying ovens are available from IR Systems and Specialty Coating Systems) or other standard processes.
- IR drying ovens are available from IR Systems and Specialty Coating Systems
- the BPA-containing coating is heated up at 80 degrees C., for 2 hours, then at 150 degrees C. for 2 hours (see example 3 in U.S. Pat. No. 4,554,342; see also J. App. Polym. Sci . (1998) 70, 2163-67).
- the BPA-binding material 30 may be layered over the BPA-containing coating in whole or in part, e.g., as a second coating.
- the BPA-binding material is an electrospun polymer film ( 31 in FIG. 1 ) that binds BPA leaching from the BPA-containing polymer to reduce or eliminate BPA contamination of the food or beverage contents of the can.
- a coating of BPA-binding material may therefore be configured to bind substantially all of the bisphenol A leaching from the BPA-containing coating.
- substantially all of the bisphenol A is meant all or at least half of the bisphenol A.
- the BPA-binding material binds at least 50%, at least 60%, at least 70%, at least 80%, at least 90%, at least 95%, at least 97%, at least 98% or at least 99% of the bisphenol A leaching from the BPA-containing layer.
- the affinity of the BPA-binding material may be intrinsic (i.e., naturally binds BPA) to the material, or it may be imparted to the material by a method such as molecular imprinting using a bisphenol A compound.
- bisphenol A compound or “BPA compound” is meant either bisphenol A itself or a compound that sufficiently mimics the structure of bisphenol A so as to impart bisphenol A-binding affinity to the polymer.
- bisphenol A compounds generally include the bis-4-hydroxyphenylmethane skeleton and its saturated or partially saturated analogs,
- Such bisphenol A compounds include without limitation, bisphenol B, bisphenol C, bisphenol E, bisphenol AF, bisphenol F, 4,4′-methylenedicyclohexanol and the like.
- BPA-binding materials including, for example, chitin, chitosan (Advances in Colloid and Interface Science, Volume (2008) 143, 48-67), dextrin (including, e.g., cyclodextrin; see J. Membrane Sci . (2009) 332, 129-37), fibroin, keratin (JP 3430257), and the like. These materials be used singly, as mixtures or in combination with other polymers. As these materials are comprised of oligosaccharides or protein, they are considered safe for use in food/beverage can coatings.
- BPA binds to the BPA-binding material with a binding constant of less than about 1 ⁇ M, less than about 500 nM, less than about 10 nM, less than about 50 nM, less than about 20 nM or less than about 10 nM.
- a binding constant of less than about 1 ⁇ M, less than about 500 nM, less than about 10 nM, less than about 50 nM, less than about 20 nM or less than about 10 nM.
- the phrase “less than about” includes values about the value and less than the value.
- less than about 1 ⁇ M includes values at about 1 ⁇ M and values less than 1 ⁇ M.
- BPA-binding materials may be created by the molecular imprinting method.
- Various polymers may be imprinted with a BPA compound (as defined herein) to provide molecular imprinted polymers (MIPs) such as cellulose, cellulose acetate, cellulose acetate butyrate, lignocellulose, polyamine, N alkyl acryl amide, N vinyl pyrrolidone, triethylene glycol dimethylacrylate (TEGDMA), trimethylol propane trimethacrylate, and the like.
- MIPs molecular imprinted polymers
- Cellulosic polymers are particularly useful in the present technology as they are generally stable to heat and various solvents/liquids and are thus well-suited to the inner coating of food/beverage cans.
- cellulosic polymers provide good strength to the MIP when electrospun.
- cellulosic polymers are an abundant natural fiber that is inexpensive and easy to obtain and use.
- MIPs for use in the present technology may be produced using methods known in the art (see, e.g., Ikegami et, al. “Synthetic polymers adsorbing bisphenol A and its analogues prepared by covalent molecular imprinting using bisphenol A dimethacrylate as a template molecule” Anal. Bioanal. Chem . (2004) 378: 1898-1902).
- the BPA compound is the template molecule which is to be imprinted in the polymer.
- Methods of preparing the MIP may be adapted from Kubo, T., et al. J. Chromatogr. A (2004) 1029, 37-41; and Kubo, T., et al. J. Chromatogr.
- the template molecule and polymer are crosslinked and polymerized using an appropriate cross-linking agent such as chloroform and UV irradiation described in such a reference above.
- the template molecules are then removed from the polymer to leave the imprint of the BPA compound.
- the polymer is hydrolyzed with appropriate agent, such as NaOH.
- the BPA-binding material may include only the material or mixture of materials described above which have an affinity for BPA, or it may be a mixture with other suitable polymers. Such mixtures may be produced so long as the BPA-binding material and polymer are soluble in a common solvent (so that they may be electrospun together).
- Such polymers include but are not limited to poly-vinylidene fluoride (PVDF), poly(acrylonitrile-co-methacrylate), polymethylmethacrylate, polyvinylchloride, poly(vinylidenechloride-co-acrylate), polyethylene, polypropylene, nylons such as nylon 12 or nylon-4,6, aramid, polybenzimidazole, polyvinylalcohol, polyvinyl, pyrrolidone-vinyl acetate, poly(bis(2-(2-methoxy-ethoxyethoxy))phospazene (MEEP), poly(propyleneoxide), poly(ethyleneimide) (PEI), poly(ethylene succinate), polyaniline, poly-(ethylene sulfide), poly(ethyleneterephthalate), poly(ethylene oxide), poly(vinyl acetate), poly(oxymethylene-oligo-oxyethylene), SBS copolymer, poly(hydroxyl butyrate), collagen, poly(lactic acid), poly(glycolic acid),
- the coating of bisphenol A-binding material is formed by electrospinning to yield a nanofiber structure.
- the electrospun coating has a micro porous structure (see FIG. 2 , for example) which provides a large surface area and is hydrophobic. Therefore, this coating both captures BPA from the BPA-containing polymer, and keeps the food/beverage contents in the can from contacting the BPA-containing coating.
- Electrospinning of the BPA-binding material may be carried out using methods known in the art such as, for example, those described in US 2002/0100725 and U.S. Pat. No. 7,390,760.
- the BPA-binding material is dissolved in one or more solvents to create a coating solution.
- solvents including, without limitation, water, acetone, chloroform, ethanol, isopropanol, methanol, toluene, tetrahydrofuran, benzene, benzyl alcohol, 1,4-dioxane, propanol, carbon tetrachloride, cyclohexane, cyclohexanone, methylene chloride, phenol, pyridine, trichloroethane, and acetic acid, trifluoroacetic acid (TFA), and the like.
- TFA trifluoroacetic acid
- the concentration of the BPA-binding material in the solvent will depend on the type of the nanofiber desired.
- the amount of BPA-binding material in the coating solution may range from about 0.1 wt % to about 40 wt %, from about 1 wt % to about 35 wt %, from about 5 wt % to about 20 wt %, from about 0.1% to about 5 wt %, depending on polymer used and fiber to be produced.
- concentration of BPA-binding material in the coating solution may range from about 0.1 wt % to about 40 wt %, from about 1 wt % to about 35 wt %, from about 5 wt % to about 20 wt %, from about 0.1% to about 5 wt %, depending on polymer used and fiber to be produced.
- additional properties of the nanofiber formed such as thickness, diameter and density may also depend on the electrospinning condition such as voltage, time of coating, temperature, and the like.
- the voltage applied during the electrospinning may range from about 1.0 kV to about 30 kV, from about 5 kV to about 30 kV, or from about 10 kV to about 30 kV.
- the thickness of the coating may be controlled in the range from about 1 ⁇ m to 1 mm, about 1 ⁇ m to 500 ⁇ m, about 10 ⁇ m to 300 ⁇ m, and about 10 ⁇ m to 200 ⁇ m.
- the diameter of the nanofiber may range from about 5 nm to about 200 nm, from about 5 nm to about 100 nm, from about 5 nm to about 50 nm, from about 10 nm to about 200 nm, from about 10 nm to about 150 nm, or about 10 nm to about 100 nm.
- Machines for electrospinning are commercially available, such as, e.g., the NEU from Kato Co. Alternatively, the machines described in U.S. Pat. No. 6,713,011 (incorporated by reference in its entirety herein) may be used.
- the electrospinning may be done before or after shaping the can. It may also be carried out sequentially after the BPA containing layer is formed.
- can stock (a metal sheet with a BPA-containing polymer coating) is coated with nanofiber formed from the BPA-binding material using one or more electrospinning machines or an electrospinning machine with a plurality of spinning nozzles. The can is then formed from the now double-coated can stock using conventional methods.
- a food or beverage can may be coated with a single coating composition that is a mixture of the BPA containing polymer and the BPA binding material.
- the BPA-binding material will scavenge any free BPA from the BPA-containing polymer and reduce or prevent its migration into the can contents.
- the same BPA-binding materials and BPA-containing polymers described above may be used for this coating also.
- the ratio of the BPA-binding material to BPA-containing polymer in the coating composition may range from about 5 weight percent (wt %) to about 80 wt %, from about 10 w % to about 80 w %, from about 20 w % to about 70 wt %, from about 30 wt % to about 70 wt %, or from about 40 wt % to about 70 wt %.
- Such compositions may be prepared according to the procedures known in the art such as those disclosed in JP 2009-242556 and JP 3430257. The same procedures and conditions for electrospinning of this coating as described above may be used.
- a metal can with an epoxy coating is prepared in accordance with the procedures set forth in U.S. Pat. No. 3,960,979 (herein incorporated by reference in its entirety) as follows.
- a polyester diol is prepared as follows.
- a suitable vessel equipped with thermometer, stirrer, condenser, and a nitrogen inlet, are placed the following materials: ethylene glycol, 47.0 grams, 1,2-propylene glycol, 19.0 grams, adipic acid, 138.7 grams, 0.02 gram of phosphoric acid, and 0.005 gram of tetraisopropyl titanate (available from E. I. du Pont de Nemours and Co. under the trade name of Tyzor TPT).
- the contents of the vessel are heated at approximately 200° C. until the acid number is reduced to one or below. This takes approximately 5 hours.
- polyester diol, poly (ethylene 1,2-propylene adipate) will have a hydroxyl number of about 205, viscosity at 60° C. of about 110 centipoises, and a molecular weight of about 1120.
- reaction vessel In a suitably equipped reaction vessel is placed approximately 20% of the following solution: methyl methacrylate, 684 grams, ethyl acrylate, 1008 grams, acrylic acid, 108 grams, benzoyl peroxide, 5.4 grams, iso-propanol, 231 grams, 2-methoxy-1-ethanol, 540 grams.
- the contents of the reaction vessel are heated to 105° C. under a nitrogen purge.
- the remaining 80% of the above described solution is then added to the reaction vessel over a three-hour time period.
- the contents of the reaction vessel are maintained at 105° C. for an additional approximately one hour.
- the resulting polymer will have a composition of methyl methacrylate/ethyl acrylate/acrylic acid (38/56/6 wt/wt/wt).
- the polymer will have a number average molecular weight of about 30,000 and a weight average molecular weight of about 84,000 as determined by gel permeation chromatography.
- the formulation described in (c) above is mixed in a feed tank and pumped to 136 atmospheres (2000 pounds per square inch) through a high pressure air-driven pump to a specially designed hot-melt spray gun.
- the hot-melt gun was modified from that used in conventional hot-melt application to permit using thermosetting compositions.
- the modified spray gun includes the following features: minimal material hold up in the heated section of the gun; non-circulating material flow through the heated part of the gun, although external recirculation is possible; air-actuated nozzle control for uniform atomization and for sharp “tail-free” cut-off; and by-pass line for purging the gun when not in use.
- the can to be coated is rotated on its axis at a speed of about 2000 revolutions per minute.
- the gun is mounted on an indexing table and its nozzle is adjusted to ensure complete coverage of the interior of the can.
- the gun is actuated by an electronically operated air-solenoid for 90 milli-seconds.
- a 12-ounce D and I can is used, curing at 205° C. for 2 minutes will result in a dry coating weighing 470 mg.
- the gun is actuated for 50 milli-seconds the cured coating weight will be 250 milligrams per can.
- two-component meter-mix pumping equipment can be used with the hot-melt gun where components A and B are mixed together shortly before use or in the spray gun.
- a BPA-binding material that is an electrospun cellulose nanofiber coating may be prepared essentially as set forth in K. Ohkawa et al., “Preparation of Pure Cellulose Nanofiber via Electrospinning” Textile Research Journal (2009) 79(15): 1396-1401.
- Cellulose samples prepared from wood pulp may be purchased from Sigma-Aldrich, Japan.
- the average molecular weight Mw of the wood pulp cellulose is 36,000 to 40,000.
- the cellulose samples are dissolved in trifluoroacetic acid (TFA) at room temperature at concentrations (weight %) ranging from 4.0 to 5.0 wt %.
- the electrospinning is performed on the coated metal can of the above Example 1 at room temperature.
- the polymer solution is placed into a 3 mL syringe with a capillary tip having an inner diameter of 0.6 mm.
- a copper wire connected to the positive electrode is inserted into the polymer solution.
- a copper plate wrapped with aluminum foil is used as the collector and the collector is connected to the ground.
- a high voltage power supply (HAR-50P2, Matsusada Precision Inc., Japan) is employed to generate the electric field (0-30 kV).
- the applied voltage and the tip-to-collector distance are 15 kV and 15 cm.
- An electrospun coating of chitosans may be prepared essentially according to the procedures set forth in Ohkawa, K., “Electrospinning of Chitosan,” Macromol. Rapid Commun, 2004, 25(18): 1600-1605.
- the viscosity average molecular weights of the chitosan samples may be determined according to the method of Roberts ( International Journal of Biological Macromolecules (1982) 4:6, 374-377).
- Roberts International Journal of Biological Macromolecules (1982) 4:6, 374-377.
- two grades of commercial chitosan may be purchased from Wako Pure Chemical Industries, Ltd., Japan. The first is chitosan10 (viscosity average molecular weight, Mv 1 ⁇ 4 2.1 ⁇ 10 5 ; degree of deacetylation, 0.78), and the second is chitosan100 (Mv 1 ⁇ 4 1.3 ⁇ 10 6 ; degree of deacetylation, 0.77).
- Poly(vinyl alcohol) (PVA; degree of polymerization, approximately 2,000; Mn 1 ⁇ 4 8.8 ⁇ 10 4 ) may be purchased from Wako.
- Acetic acid (AcOH), formic acid (FA) and dichloromethane may also be purchased from Wako.
- Trifluoroacetic acid (TFA) may be obtained from Tokyo Chemical Industry Co., Ltd. All the solvents may be used without further purification.
- the electrospinning experiments are performed at room temperature.
- the polymer solution is placed into a 3 mL syringe with a capillary tip having an inner diameter of 0.6 mm.
- a copper wire connected to the positive electrode is inserted into the polymer solution.
- a copper plate wrapped with aluminum foil is used as the collector and the collector is connected to the ground.
- a high voltage power supply (HAR-50P2, Matsusada Precision Inc., Japan) is employed to generate the electric field (0-30 kV).
- the applied voltage and the tip-to-collector distance are fixed at 15 kV and 150 mm, respectively.
- PVA is dissolved in distilled water (DW) at a concentration of 9 wt %
- chitosan10 is dissolved in neat FA at 7 wt %.
- a PVA-DW solution (9 wt %) is mixed with a chitiosan10-FA solution (7 wt %) in the volume ratios 90:10, 70:30, 50:50 and 30:70.
- a chitosan100-neat FA (2 wt %, or 0.2 M AcOH) solution is mixed with a PVA-DW solution (9 wt %) in a volume ratio of 50:50.
- the mixed solutions are then subjected to electrospinning with the apparatus and parameters as described above.
- the chitosan10 is dissolved at concentrations ranging from 7 to 9 wt % in the following solvents: neat FA, dichloroacetic acid (DCA), TFA and aqueous acetic acid (0.2 M AcOH) and hydrochloric acid (0.1 M HCl), and their mixtures with methanol, ethanol, 1,4-dioxane, dichloromethane, N,N-dimethylformamide or dimethylsulfoxide were used as the solvents.
- the solvents used for dissolving chitosan10 and PVA are FA and DW, respectively.
- An electrospun coating of dextrin may be prepared essentially according to the procedures set forth in Uyar, T., et al. “Molecular filters based on cyclodextrin functionalized electrospun fibers” J. of Membrane Science (2009) 332, 129-137.
- Beta-cyclodextrin (beta-CD) may be purchased from Wacker Chemie AG (Germany). The materials may be used without any purification.
- the homogeneous clear solutions are prepared by dissolving PS and beta-CD in DMF at room temperature.
- the polymer concentration is varied from 15% to 25% (w/v) and the beta-CD content is varied from 10% to 50% (w/w) with respect to polymer.
- the polymer solutions are placed in a 1-mL syringe fitted with a metallic needle of 0.4 mm inner diameter.
- the syringe is fixed horizontally on the syringe pump (Model: KDS 101, KD Scientific), and a electrode of a high voltage power supply (Spellman High Voltage Electronics Corporation, MP Series) is clamped to the metal needle tip.
- the flow rate of polymer solution is 1 mL/h and the applied voltage is 15 kV.
- the tip-to-collector distance is set to 10 cm and a grounded stationary rectangular metal collector (15 cm ⁇ 20 cm), covered by a piece of clean aluminum foil, is used for the fiber deposition.
- the whole electrospinning apparatus is enclosed in glass box, and the electrospinning is carried out in a horizontal position at room temperature.
- the fibers collected on aluminum foil are dried at 40° C. under vacuum oven for 24 h to remove the residual solvent.
- An electrospun coating of fibroin and/or keratin may be prepared essentially according to the procedures set forth in Ki et al. J. of Membrane Science (2007) 302:1-2, 20-26.
- the pure SF (silk fibroin) and WK (wool keratose)/SF (50/50 mixture ratio) blend dopes are prepared by dissolving in 98% formic acid at room temperature for 4 h and the concentration of the SF and WK/SF dopes are 12% and 15%, respectively.
- the solutions are filtered to remove impurities.
- each dope solution is placed in a 10-ml syringe with stainless steel syringe needle (22 G) as an electrode which connected to power supply (Chungpa EMT High Voltage Supply, Korea).
- the syringe is loaded in a syringe pump (KD Scientific, USA) to control a flow rate accurately with spinning rate.
- Rolling stainless drum is used as a collector for obtaining sheet type nanofiber assemblies and grounded.
- the flow rate of dope solution is controlled to maintain a constant size of droplet at the tip of the syringe needle.
- the electrospinning condition is performed at room temperature and 60% (RH) humidity. Electric potential and distance to collector were fixed at 12 kV and 10 cm, respectively.
- An electrospun coating of fibroin and/or keratin may be prepared essentially according to the procedures set forth in Ikegami et al., “Synthetic polymers adsorbing bisphenol A and its analogues prepared by covalent molecular imprinting using bisphenol A dimethacrylate as a template molecule” Anal. Bioanal. Chem . (2004) 378: 1898-1902 as follows.
- BPA dimethacrylate is purchased from Aldrich (Milwaukee, Wis., USA). Chloroform is purified by distillation prior to use. Triethylene glycol dimethacrylate (TEGDMA) and trimethylol propane trimethacrylate (TRIM) may be obtained from Wako Pure Chemical Industry (Osaka, Japan) and are used after shaking with an inhibitor remover (Aldrich).
- TEGDMA Triethylene glycol dimethacrylate
- TOM trimethylol propane trimethacrylate
- BPA dimethacrylate-based polymers with TEGDMA (TE-P) and BPA dimethacrylate-based polymers with TRIM (TR-P) are each prepared with a different cross-linking agent, TEGDMA or TRIM, respectively.
- the preparation of TE-P is carried out as follows.
- BPA is analyzed by means of a Gilson HPLC system consisting of two pumps (models 305 and 306), an auto-injector (model 234), and a UV-visible detector (model 119); Supelcosil LC-8-DB reverse-phase column (5 ⁇ m, 150 mm ⁇ 4.6 mm i.d.; Supelco) is used with water-acetonitrile (60:40, v/v, 1.0 mL min-1) as mobile phase. The sample volume injected is 10 ⁇ L. The effluent was monitored at 260 nm.
- TEGOH Determination of TEGOH is carried out with an LC-MS system consisting of two Gilson Model 306 pumps, a Gilson autoinjector Model 231XL, and API-2000 mass spectrometer (Applied Biosystems, USA). Positive-ion mode is used for both Q1 scan and product-ion scan with an ion-spray voltage of 5000 V.
- the mobile phase is water containing 0.1% acetic acid-methanol (1:1, v/v) and the flow rate is 0.2 mLmin ⁇ 1 .
- the sample volume was 10 ⁇ L.
- TR-P particles (233 mg, containing BPA 23.4 ⁇ mol and TRIM 663 ⁇ mol) are also treated under the same conditions described above.
- the amount of BPA released is determined by means of the above HPLC system.
- Trimethylol propane (TRIMOH) in the washings is determined by means of the above LC-MS system with water containing 0.1% acetic acid-acetonitrile (1:1, v/v, 0.2 mLmin-1) as mobile phase and the sample adjusted to 0-10 ⁇ mol L-1 in analysis of TRIMOH.
- TE-PH and TR-PH are prepared for chromatographic tests under the conditions determined by the above experiments: TE-P particles (5.94 g, containing BPA 703 ⁇ mol) were heated under reflux in 1.0 mol L-1 sodium hydroxide ethanol-water solution (85:15, v/v, 300 mL) for 48 h.
- TR-PH is prepared in the same manner except for the amounts of TR-P particles (5.83 g, containing BPA 586 ⁇ mol).
- Electrospinning of the MIP may be carried out under the following conditions.
- the polymer obtained as above is dissolved in distilled water (10 wt %).
- the flow rate of polymer solution is 1 mL/h and the applied voltage is 15 kV.
- the tip-to-collector distance is set to 10 cm.
- Example 2 Three metal cans are fabricated according to Example 2 (test cans) and three metal cans are fabricated according to Example 1 (controls).
- Each can is filled with an acidic aqueous solution simulating, e.g., orange or tomato juice (pH 3-5), and which does not contain any detectable BPA.
- the cans are heated to boiling for 30 minutes.
- samples of the water from each can are assayed by HPLC for dissolved BPA using the system described in Example 6.
- the water from the cans without the electrospun coating will show a significant concentration of BPA, whereas the water from cans with the electrospun coating will show little or no detectable BPA.
- a range includes each individual member.
- a group having 1-3 cells refers to groups having 1, 2, or 3 cells.
- a group having 1-5 cells refers to groups having 1, 2, 3, 4, or 5 cells, and so forth.
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Abstract
Description
Claims (20)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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PCT/US2010/049808 WO2012039708A1 (en) | 2010-09-22 | 2010-09-22 | Can with bisphenol a capture system |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/US2010/049808 A-371-Of-International WO2012039708A1 (en) | 2010-09-22 | 2010-09-22 | Can with bisphenol a capture system |
Related Child Applications (1)
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US13/683,894 Continuation US9221583B2 (en) | 2010-09-22 | 2012-11-21 | Can with bisphenol A capture system |
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US20120067763A1 US20120067763A1 (en) | 2012-03-22 |
US8337967B2 true US8337967B2 (en) | 2012-12-25 |
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US13/201,607 Expired - Fee Related US8337967B2 (en) | 2010-09-22 | 2010-09-22 | Can with bisphenol A capture system |
US13/683,894 Expired - Fee Related US9221583B2 (en) | 2010-09-22 | 2012-11-21 | Can with bisphenol A capture system |
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US13/683,894 Expired - Fee Related US9221583B2 (en) | 2010-09-22 | 2012-11-21 | Can with bisphenol A capture system |
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WO (1) | WO2012039708A1 (en) |
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US11051529B2 (en) | 2015-01-13 | 2021-07-06 | The Decaf Company, Llc | Programmable polymer caffeine extraction |
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US9315619B2 (en) | 2013-01-29 | 2016-04-19 | International Business Machines Corporation | Binding Bisphenol A in a polycarbonate container |
CN107144499A (en) * | 2017-05-16 | 2017-09-08 | 东莞出入境检验检疫局检验检疫综合技术中心 | The research method of bisphenol-A Transport in simulated body fluid in ABS plastic toy |
US11492737B1 (en) * | 2021-08-19 | 2022-11-08 | United Arab Emirates University | Method for dissolving lignocellulosic biomass |
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